


Horizons

by thegrendel



Category: Original Work
Genre: Anal Sex, F/M, Gay Sex, Heterosexual Sex, M/M, Sex Change
Language: English
Status: Completed
Published: 2018-08-22
Updated: 2018-08-22
Packaged: 2019-07-01 04:29:46
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,583
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15766626
Author URL: https://archiveofourown.org/users/thegrendel/pseuds/thegrendel
Summary: Can a thoroughly gay man, a bottom in fact, flip over and become straight? Sure, if you make the intuitive leap that making love to a woman is not all that much different than making love to a man. It's just a matter of expanding your horizons. And, after all, a hole is a hole is a hole.





	Horizons

Bobby knew his place in the world. He was a bottom. He was the one who  
got on his hands and knees and presented his ass. And mostly, he liked  
it that way.

Oh, once in a while he'd switch and be the one doing the inserting.  
Bobby was actually quite a skilled cocksman, and he enjoyed the turnabout.  
But bottoming was his real talent. "You're a natural born receptacle,"  
Norm would tell him. "Your butt was made for fucking."

On a hot day in July they were out swimming and sunbathing. It was an  
equal opportunity beach, with both straights and gays out in force. This  
made for quite an interesting mix.

A sudden wave caught Bobby from behind and knocked him off his feet. He  
was spitting out salt water and sand as Norm helped him up and slapped  
him on the back. A group of laughing women walked by.

"Hey, look at them depraved dollies, Bobby, old boy. Betcha you wouldn't  
know what to do with that kind of meat."

"You think? Look, my equipment is every bit as good as any their boyfriends  
have got. Who says I couldn't . . . ?"

"You're a wacko, Bobby. We've been together -- what -- two years now?  
Your _ass_ is what I stick my equipment into. And you're saying you  
could make it with a _woman_? Whoa, baby, dream on!"

"Damn it, Norm. I'll prove it! What's it worth to you if I can get one of  
them girlie girls in the sack?"

"Bobby, old fellow, if you can pull off _that_ stunt, I'll let you  
top me every day for a month straight. How's that hit you?"

 

Well, why not? He knew the right moves, more or less. Hey, sticking it  
into a cunt couldn't be all that different than into an asshole, could  
it now? Only trouble was, that was virgin territory for Bobby. He had  
never even _kissed_ a woman.

"Hey! 'Scuse me, ladies. Would one of you care to volunteer for a  
scientific experiment?"

A tall blonde turned around and favored him with a steely-eyed glare.  
Her two friends giggled.

"Now that's the sorriest excuse for a pickup line I've heard in years.  
What next? You're gonna offer me a role in a movie?"

"Truly, Julie. It's in the name of science. I -- "

"You've got the wrong woman. Julie's the one who ran off with the crown  
jewels. _Your_ crown jewels. Get lost, asshole." Blondie and her  
friends began to walk off.

"Wait! I know the secrets! I can -- "

 

Norm tried to cheer him up. "Hey, sweet guy, you can't just walk up to  
a woo-man and expect her to lose her heart to little old you just on  
account of your pretty blue eyes. There's a whole song and dance you  
gotta go through. Taking them out to dinner, entertaining, and all that  
bullshit. More trouble than it's worth. Believe me."

Bobby was thinking on it later that afternoon. He was flat on his stomach  
with a beach towel underneath. They were in a secluded cove behind the  
seawall. Norm was on top of him -- deep inside him in fact.

"Damn it, I _do_ know the secrets. I know as much about ass-fucking  
as anyone. I could bring a woman unimaginable pleasure like that. If  
they'd just listen . . . "

"What's that you're mumbling, Bobbie? Want me to pump faster?"

"No. Push all the way in. Deeper. Yeah, that's good. Now stretch out  
flat on my back and don't move. Let's see if I can make you come just  
by squeezing. I'm gonna milk you dry and make you beg for mercy."

Just as Bobbie felt Norm shudder and groan to the accompaniment of the  
familiar throbbing and wetness high up in his gut, he thought he heard  
clicking sounds. Turning his head to one side, he saw a woman standing  
there. She was snapping pictures. It was Blondie.

"Would you mind holding that pose, darlings?" she said. "I'm a  
photojournalist doing a spread on modern mating customs."

As Bobbie and Norm struggled into their swim trunks, the woman continued  
to shoot. Norm walked over to her and held out his hand for the camera.

"What's your game, dame? Blackmail? Or maybe you're just a plain vanilla  
peeping tom. Give."

"It's the other guy I'm interested in, the one you just finished  
shtupping. Shove off, dickhead, so I can talk to him for a moment or two,  
and I'll let you have the roll of film afterwards. Or I can send you a  
set of custom prints, if that's what you'd prefer."

Norm spit into the sand, then walked around the seawall, leaving Bobbie  
alone with her.

"Why didn't you just come right out and say you were a queer, 'scuse me,  
gay interested in some female booty? That might even have worked. It  
so happens that I've been fascinated by anal for a good long while. My  
boyfriend won't go near my butt, thinks it's dirty. Goes without saying  
that he won't let me near his own, either. I'm Lissa, by the way."

"Pleased to meet you. I'm Bobby."

"Well, Bobby, what say we get together some time and discuss topics of  
mutual interest?"

 

Bobby's hands were shaking. He felt like a teenager on his first date.  
He had doused himself with way too much of Norm's best cologne and the  
too-tight shirt collar was chafing him. There were beads of sweat  
trickling down his face. He stood in front of the cold, uncaring  
intercom box.

_C'mon, fella, push that button. The worst that could happen is that_  
she's been putting you on and gave you a phony address. So what? A little  
humiliation never killed anybody. 

The loud buzz almost stopped his heart.

"Come on up, Bobby. Sorry to have startled you. Saw you on the videocam  
as you walked into the outer lobby. It's 7E, on the seventh floor."

The door opened at his knock. Lissa had on a casual outfit -- shorts and  
a halter top. Bobby felt self-conscious in sports jacket and tie.

"Drinks?"

"No thanks, Lissa. My friends say I'm spaced-out out even when stone  
cold sober."

"I can understand why. Say, you must be awfully hot in that monkey suit.  
Wait. I'll get you something comfy you can slip into." She disappeared  
into the next room.

Bobby felt much better in the gray silk bathrobe. It was three sizes too  
large. Must be her boyfriend's.

She had on a matching robe, but in a bright shade of magenta.

"So, let's talk. I can't say I'm much interested in you as a person  
\-- sorry about that -- but fill me in on what you know about anal  
lovemaking."

"Since you have a disconcerting habit of getting straight to the point,  
Lissa, let me ask you what _you_ know about it, so I know where  
to start. Have you ever actually done it?"

"About three boyfriends ago I gave it a shot. The guy had never heard  
of lube, and anyhow, he was a clumsy idiot. All his fumbling efforts  
only got him partway into me before he shot his wad. It hurt a lot,  
and that spoiled it for me for a good while. Since then, well, I've done  
some reading about it, but there's been no action."

"Yes. And why are you so obsessed with, well, sodomy?"

"Are we getting biblical now? Or just witty? For a gay man you seem to  
be pretty damn sure of yourself when you're in the company of a woman.  
I like that.

"You see, Bobby, I don't really get very much out of so-called normal sex.  
Actually, the only way I can come is by rubbing my clit. (You _do_  
know what a clit is, don't you?) Even then I have to stick a finger up  
my . . . my ass. I'm highly sensitive in there. It seems to trigger  
me somehow, to push me over the edge. Now I want to feel a real cock  
. . . inside me, inside that place."

"As it happens, Lissa, I've done a few asses in my time. Mostly, though,  
I get my own ass done, as you might have figured out by now. Anyhow,  
I know all sides of the deal, top and bottom both. For a start, let me  
show you a couple of relaxation techniques."

 

"That's a good girl, push outward, as if you were on the pot and doing  
a 'number two.' Gently. No need to strain. This unlocks the sphincter  
ring. See how easily a finger slips into you. Now another. It's Mother  
Nature's little reflex for expelling waste out of your gut. It also  
opens you up . . . and gives access to the dark inner mysteries."

"Dark mysteries, huh? You have the soul of a poet. You know that, Bobby?"

"The poet is exploring the darkest of your mysteries. Now I'll stretch  
you by rotating the two fingers inside you. How does that feel?"

"Not too shabby . . . actually quite nice. Kind of like being gently  
pried open. Wide open. What's next -- being turned inside out?"

"Let's not rush things. I'm lubing you inside, as well as stretching and  
loosening you at the entrance. Don't like to use this cheap petroleum  
jelly stuff, but that's all you had in that fancy medicine cabinet of  
yours. It'll work okay for now, though."

"You still have a hand free, don't you, Bobbie? Use it. Reach around and  
rub my clit. That's a good boy. Ah, yes. Faster. Oh, that's good. _Ah!_ "

She had reached insertion readiness, but Bobby had a slight problem.  
He had gone limp. Performance anxiety. Being with a woman for the very  
first time can do that. Then something occurred to him.

"Lissa, I could use a little help now. Would you mind doing to _my_  
ass what I just did to yours? Here's the lube.

"Yes, now another finger. A third. Plunge in and out. Deeper and harder.  
Yes!"

Bobby visualized being fucked in the ass, and his imagination magically  
transformed Lissa's fingers within him into Norm's cock. His own began  
to rise.

"I'm set, Lissa. Need any more preliminaries?"

In answer, she got to her hands and knees, then lowered her head onto  
the bed. Blonde corkscrew curls overflowed the pillows and gleaming round  
buttocks stuck up into the air. Late afternoon sunlight filtering through  
the window shades threw black-and-white stripes across her naked back.

He had been right all the time. Inside, a woman's ass felt no different  
than a man's.

Lissa's opening had dimpled inward as he pressed the tip of his cock  
against it ( _just like Norm's_ ), then it had yielded, and his shaft  
slowly disappeared inside her, an inch at a time. She was a bit tighter  
inside than he was accustomed to, but that would change as her sphincter  
and rectum stretched with repeated use. Her gut seemed to have a ripply  
feel to it, and that gave a textured friction sensation. When she came,  
there was a heavy flow of fluid from her pussy -- a female ejaculator  
. . . how about that! -- rather than from a non-existent cock. Bobby  
felt a peculiar kinship to her, since, like himself, ass-fucking alone  
could bring her to orgasm.

He fell asleep with his head buried in her soft, fragrant breasts . . .

. . . and awoke with a kiss on his lips and her hand on his cock.  
Morning erection. Apparently she had plans for it.

"In my pussy this time, darling. Quick, hop in the shower and wash off  
. . . but don't lose that hardon. It's mine."

She was waiting for him as he came out of the bathroom. Down, on her  
hands and knees on the hall carpeting. Almost like yesterday.

Bobby was a little afraid. This would be his "first time" -- the first  
time in his life that he would do it in the "normal" way. The final  
barrier to becoming a full and complete _man_.

Looking at her buttocks tilted high in the air, he could squint a little  
and imagine the pussy right there in front of him was really an asshole.  
That made it less threatening. Think of it . . . as ass-fucking her in  
the cunt!

Strangely enough, she felt just about the same inside that other opening.  
Possibly a little looser . . . maybe a teensy bit smoother . . . not quite  
as burning hot inside. He reached around to hold her breasts. Just for  
fun, he tweaked a nipple. She shivered, then groaned. He had a sudden  
inspiration.

He pushed a finger into her ass, and her entire body convulsed. Rhythmic  
spasms clutched his cock as she came, and he could no longer hold back.  
Bright light exploded behind his eyes. ( _My gosh! This might even be  
better than ass-fucking._ )

 

"I could easily get used to this, Lissa. Making love to a woman, I mean.  
Or maybe what I really mean is making love to _you_. I don't know  
if . . . if things can ever be the same between me and Norm. You've  
_ruined_ me, damn you."

"In spite of myself, I'm starting to get strong feelings for you, too,  
Bobbie boy. Kiss me, you fool!"

 

"You know what I really want, darling? A family of my own. . . . I think  
maybe at heart I'm really just an old-fashioned woman. . . . A kid, or  
maybe two, or even three. Backyard barbecues. Wiping runny noses. Drying  
tears. Soothing minor hurts. Snuggling under the covers in a king-size bed  
after all the kids -- and the dog and the cat -- are asleep. Raindrops  
pattering on the bedroom window. A home, and security. A normal life.  
And someone I love . . . to spend it with. Someone like you."

"Lissa, hearing you say those words to me feels so good that it hurts.  
It tears me up. But, what part could I possibly play in this dream of  
yours? What about your boyfriend?"

"That worthless bum hardly even knows I exist any more. He hates the way  
I look. Says I'm way too fat and my ass is gigantic. We haven't made love  
for weeks. All he really cares about is his beer and the football games  
on TV. He's just a slug, an unconscious lump of idiot male flesh. And if  
that weren't enough, he's a flaming momma's boy. All he really has going  
for him is that great bod of his. But, you know, yours is every bit as  
good. And, unlike him, you have a mind to go with it." She reached for  
his hand. "But what about _your_ boyfriend?"

"We've had a nice thing going for a couple of years. We're pretty good  
friends and we get along okay. Even the sex is okay, mostly. But there's  
no real closeness. If it weren't for the sex, actually, we'd be more  
like roommates than lovers. I think I'm long past ready to move on to  
new horizons."

"Could it be that I'm on your horizon, Bobby?"

 

After a relatively civilized discussion, Bobby moved his things out  
of the house he and Norm had shared and into Lissa's apartment. Lissa  
went shopping for a dildo harness, and she attends quite assiduously to  
_all_ of Bobby's various needs. They're very compatible physically,  
and of late have been talking seriously about marriage.

Norm found a new roommate. Hobart, Lissa's previous boyfriend, had finally  
outworn his welcome at his parents' house -- after 30 years -- and was  
desperate for a place to stay. He and Norm get along splendidly. They  
have a great time on the beach, and have been observed sunbathing in  
the nude in a certain secluded cove behind the seawall.


End file.
